By Rishika Sharma, on October 12, 2022

Pack like a star and travel in style: Insider tips from a celebrity stylist and red-carpet pro

Have you ever seen a snap of a well-rested and somehow-still-glamorous celeb stepping off a 12-hour flight and wondered, “How do they look so good?” Well, celebrity stylist professional bag-packer Jennifer Michalski-Bray might just have the answer for you.

Jennifer is our guest on this week’s episode of Out Travel The System. She’s a sartorial genius who has worked her magic on countless editorials, front covers, red-carpet events, and NYC Fashion Weeks, not to mention the TV series Gossip Girl. A packing pro, part of Jenifer’s job is to prepare outfits and luggage for her high-flying clientele when they set off for whirlwind press junkets. As frequent traveler herself, Jennifer is a self-declared hater of checked-in luggage and has become an expert at packing away-from-home wardrobes that have their wearers looking constantly, effortlessly put-together… without needing oversized suitcases to carry everything.

It’s a priceless skill to have, especially at the moment. While 2022 will certainly hold a special place in many people’s hearts as the year travel came back, for some it will also, unfortunately, be remembered as the year of lost luggage. Who could forget the shocking image of a Delta flight from London to Detroit carrying nothing but one thousand stranded bags, or a graveyard of abandoned suitcases at Heathrow Airport?

While the overwhelming majority of travelers are soon reunited with their belongings, losing a bag is always a pain – and even more so when it happens on this kind of scale. In fact, the Office of Aviation Consumer Protection reports that over one million pieces of luggage were lost this summer by US airlines – and in May alone, nearly 240,000 bags were mishandled by US carriers. That’s s over half the number of bags that were checked in that month, meaning roughly one-in-two travelers temporarily lost their carefully curated, Insta-worthy outfits, precious souvenirs, and basic undergarments.

While the situation will almost certainly improve as the travel industry continues to recover, it never hurts to up your carry-on packing and travel-preparation game. So we asked Jennifer for her essential must-packs and must-dos:

A hand-held steamer
“One thing that will keep you looking polished is a handheld steamer. When you’re rummaging through your suitcase and find that your dress is a wrinkly mess, a handheld steamer will iron it all out in 45 seconds, and you’ll look like you’ve just walked out of the store wearing off-the-rack. It also basically cleans the outfit for you by getting rid of any germs, so it’s like washing your shirt. I’ll never travel without it. My favorite brand is Philips and they have some that heat up in 30 seconds.”

“Topstick – or more accurately, toupee tape – is a great quick fix for things. Like, if you have a button-down shirt that keeps opening at the bust area, Topstick will help you close it where you want without you having to carry a small sewing kit to add in stitches. Or if you have straps that keep falling, stick them onto you and you’ll be set if you can’t make permanent adjustments.”

Face masks
“Not the kind we’ve all been wearing throughout the pandemic – these are the skincare kind. And even though people might stare, I love to use a mask on a flight. It might be an extra thing to carry but it really helps to prevent my skin from drying out, so I just slap it on and chill out for the flight. Rodial is my preferred brand.”

Travel socks
“Aside from compression socks, which are a must for long-haul flights, I carry a pair of cashmere blends from Raey. They keep my feet warm from the air-con and they’re durable too.”

Pack tonally
“Packing tonally is the key to being more concise. Wearing neutrals or dressing tonally allows you to mix and match different pieces, so that way you only have to pack eight items instead of 16.”

Multi-use items
“Don’t pack a pair of shoes that only matches one outfit. Shoes should match everything in your case and allow yourself no more than three pairs. For my male clients, I’ll also pack in one belt that will go with various outfits too. And another tip is to invest in matching sets – The Frankie Shop in particular makes high-quality shirt and shorts co-ords. That way you could use the oversize shirt over a bathing suit as a cover-up too or wear it not only with the matching shorts but with pants. Button-down oversize shirts are all the rage right now because they’re so versatile.”

Layer up
“I will always be on the plane in layers because the plane is always cold. And this way, not only do I have more room to pack if I’m only bringing carry-on, but for cooler temperatures I don’t need to bring chunky knits that will take up more space. I’ll wear my biggest shoes so they don’t take up space in my luggage and I’ll wear black thermals or I have this amazing Wolford bodysuit which I’ll wear under a cardigan or jacket – something that will match all the outfits that I’ve packed.”

Roll it
“A good space-saving technique is to roll your clothes so you can fit more into your suitcase rather than if you fold them. And you don’t have to worry about wrinkles because of the steamer.”

Use garment separators
“I love packing cubes, but for clients I have looks packed into individual garment bags, which will also include all the accessories within it so it’s easy to find what goes with what. It’s a technique from my time working on Gossip Girl, and this way everything is laid out perfectly.  When I pack for myself, I have a handy jewelry cube so I can easily pack accessories that I can wear across all the outfits that I’ve packed.”

You can find more of Jennifer’s hacks and tips on Instagram. Make sure you also check out the fantastic packing guide she created especially for us.

She also made us this great downloadable guide as well.

Got your own packing tip or want to share your vacay OOTD with us? Tweet us and tag your snap #ExpediaPic.

Want to learn more?

Listen to the podcast now, check out the complete transcript below, or catch the full conversation on Spotify or Apple.

Nisreene Atassi, Expedia Global Head of Social Media, and host: I’m Nisreene Atassi and this is Out Travel The System. Today we’re going to tackle the age-old question of whether to carry-on or check a bag. We’ll talk trends…

Christie Hudson, head of Expedia PR for North America (sound bite): Nearly 240,000 bags were mishandled by airlines during just the month of May

Nisreene: ..hear from some serious experts…

Jennifer Michalski-Bray, celebrity stylist and travel expert (sound bite): I am a fashion stylist. I work with a lot of celebrities and VIPs. I am very confident that I know the ins and outs of packing.

Nisreene: ..and really get down to business.

Jennifer: They’re so tiny now too. It’s so worth the space that they take up. They’re cheap too.

Nisreene: Here we go.

[Musical interlude]

Nisreene: So when we were brainstorming for episodes we were going to do for this season and we started talking about gear, I had one colleague who was really a big source of inspiration for this particular episode. She started to describe to me how she travels economy but makes it a first-class experience. And I really sort of started to dig in and ask her why, and she started to tell me all these crazy things she brings with her. A blow-up ottoman for her feet, fancy pillows, a down comforter blanket that packs up super, super tight. She really started to make it seem like the travel she was doing was not only incredibly comfortable, but she made it sound pretty easy. Now, that all sounds super amazing, and having a down comforter on a flight, I feel like, is absolutely top-notch. But that probably, for some people, might seem like kind of a lot of stuff to carry around. So for this episode we really wanted to try to understand not only what travel gear may help make your trip a little bit easier, but also about the type of stuff that you might pack. So today we’re tapping into celebrity stylist and fashion expert Jennifer Michalski-Bray to understand if it’s really worth including those multiple outfits that you might never end up wearing. Does that happen to you? It’s definitely happening to me, but hopefully not anymore after listening to this episode.

But first, let’s hear the trends. Our lovely data correspondent Christie Hudson is here to talk about how travelers are packing these days and, of course, what they’re carrying. Hi, Christie! Welcome back.

Christie: Hi.

Nisreene: All right, Christie. So what are we talking about this week? What are the trends in this space and what are we seeing?

Christie: So I don’t mean to scare anybody, but I just saw a report issued by the Department of Transportation earlier this summer, and it said that nearly 240,000 bags were mishandled by airlines during just the month of May. And to contextualize that number for you, that’s over half of all the bags that were checked that month. So that’s a pretty startling number.

Nisreene: That is really, really startling and just kind of insane. That’s a one-in-two chance that month that you would have lost your luggage, which I’m sure could create so much stress for travelers.

Christie: Right. And, unfortunately, it’s just a reality of air travel right now. Just like airlines have been struggling with all sorts of operational challenges, they have staffing issues that impact bag handling.

Nisreene: All right, so what can we do as passengers to help mitigate this?

Christie: There are some things, as a passenger, that you can do. The first one is obvious, but not always doable, and it is to just pack light, go with a carry on, because if you don’t check a bag, they can’t mishandle it, right? But that’s not always an option for us. We all know times when a carry-on won’t cut it. For example, I’m going on a trip next week. I have to pack for two destinations. I have to pack for both work and leisure. And I’m going to Nashville to hang out with some girlfriends, and my cowboy boots just aren’t going to fit in a carry-on. So I have to check a bag. And there are some things that I would suggest you do in order to make sure you have the best experience. First off, don’t put anything really fragile or valuable in your checked luggage. Things like expensive cameras or cash, for example. These items aren’t likely to be covered by the airline’s policies if your bag does get lost or if items get damaged or stolen. Secondly, I would highly recommend packing a little back-up bag for yourself that you can put into your carry-on. So think a couple of pairs of underwear, a change of clothes, any prescriptions that you need on a daily basis. That way you have some security if your bag gets delayed or lost.

Nisreene: Yeah, I mean, that kind of seems like a no-brainer. And, frankly, I feel like that’s something I’ve started doing recently once I started to see a lot of these issues popping up with bags. It’s kind of a pain because you don’t want to carry all this additional stuff, but given the statistics and what’s happening out there, it’s, frankly, a really smart way to keep yourself protected a little bit and reduce a bit of that stress if your bag does get lost.

Christie: That’s something I would never have done before. I am 100% doing that for this trip I have coming up.

Nisreene: What else are you seeing?

Christie: If you want some extra assurance, we’ve seen some really great stories from people using those personal tracking devices. So AirTags and Tile, those can be paired with an app on your phone and then put inside your luggage and it’ll show you where your bag is. That way, if the airline can’t locate your bag, you can help them with that and they might be able to get it back to you sooner.

Nisreene: So how much do those devices cost? Are they pretty expensive or are they relatively affordable?

Christie: The AirTag is, like, 30 bucks for one, or you can get a set of, you know, four for a little bit more than that. And I know the Tiles probably run somewhere similar. So pretty affordable.

Nisreene: Yeah. I mean, that feels totally worth the investment to me, because it’s obviously going to give you more of that peace of mind, which we know is critical when you’re traveling. Okay, so what if your checked bag ends up getting lost or delayed? Then what?

Christie: So if your checked bag is lost or delayed, keep in mind that the airline does owe you some compensation. So they’re required to compensate you for the bags’ contents up to a maximum amount of around $3800 for domestic flights and around $1800 for international. And the airlines can also reimburse you more than that, but they aren’t required to. So make sure you claim for the maximum amount that you think your bag is worth if it gets lost. They’re also required to reimburse you for any checked baggage fees that you paid. And then, if your bag is delayed, you’re also entitled to reimbursement. If you have to spend money out-of-pocket to replace some essentials while you wait for your bag to be reunited with you, they have to reimburse you for that as well.

Nisreene: That is so good to know, because… I didn’t realise that they had to reimburse you for that kind of stuff. I assumed if they did find your bag, they wouldn’t reimburse me for anything. So that’s really, really good information to hear.

Christie: If in doubt, ask the airline. If you have to take a cab to get back to the airport to go pick up your bag because it was delayed, I would ask to be reimbursed for that.

Nisreene: Such a great tip. Thanks, Christie.

Christie: You got. It. Happy travels.

[Musical interlude]

Nisreene: So I’m historically a chronic overpacker and probably the worst packer on the planet. I’ve always forgotten something, I always have too much of one thing and not enough of another. It’s constantly a stressful situation for me, which is why I’m so excited that my guest today is actually an expert in packing. She literally packs for a living. Okay, well, she’s packing the latest trendy items for celebrities who might be appearing on the red carpet. She has not only some of the best tricks of the trade, but some great advice on best travel gear she feels can make travel both chic and comfortable.

Hi, Jennifer. Nice to meet you. Thanks for coming on the show today.

Jennifer: Thanks for having me. I’m so excited to be here.

Nisreene: Tell me a little bit about your background, because I feel like you live a fabulous life and I just need you to validate that.

Jennifer: Oh, well, I am a fashion stylist. I work with a lot of celebrities and VIPs, as well as magazine styling. So I am, like, very confident that I know the ins and outs of packing. I’m constantly either living out of a suitcase or packing a suitcase for someone else, whether it’s for a photoshoot… I have, like, eight suitcases with me sometimes, because, you know, you never know what the model is going to want… what the model will look like on set, and so you want options. Or, you know, with a celebrity, it’s normally just one suitcase packed to the brim, full of all the different looks that they’ll be wearing on like a press junket. So I feel like I know how to pack for all different occasions, including my own travels.

Nisreene: How many times a year would you say that you, like, actually travel?

Jennifer: I would say at least once a month, if not more. So I’m on the road a lot, and that doesn’t even count local photoshoots that are in the same country that I live in, which is England. I feel like I’m always living out of a suitcase. I still haven’t mastered – when it’s my stuff and I don’t have to unpack it, it stays in my suitcase forever and ever and ever until my next trip.

Nisreene: There are definitely two kinds of people in the world. You either unpack right away or you don’t unpack until you are, like, actually forced to do so.

Jennifer: Yeah.

Nisreene: So as a stylist, how important would you say, like, as you’re sort of packing and traveling, to make sure that you’ve got everything you need both for the trip, but then, also, what about your travel outfits and things like that?

Jennifer: So, basically, I have a set of essentials that I keep in a little bag that I pack for my clients and myself. And these are things that I will never travel without, like a handheld steamer. I always have that no matter where I travel, because that’s one thing that I think will keep you looking polished. If you just get off a flight and you rummage through your suitcase and everything’s all wrinkled, a steamer, just a quick shot… You know, there’s 30-second steamers. Philips is my favorite brand for portable handheld steamers. They heat up in 30 seconds, and then just a quick once-over – you know, 45 seconds of your time – and your dress is no longer a crinkled mess and you look great. You look like you just walked out of the store wearing, you know, an outfit off the rack instead of just out of a suitcase off a plane. So that’s, like, my number one tip I tell everyone and I always pack a portable steamer for my clients. If they’re going to, like, a press junket, that will be in their luggage to make sure that, you know, they can do any touch-ups.

Nisreene: How bad is it, Jennifer, that I use my flat iron, sometimes, when I’m traveling, to iron my clothes?

Jennifer: I mean, sometimes it’s easier, actually, than ironing. I hate ironing more than anything. So my husband hates this about me. He’s like, you know, “I have a stylist wife who refuses to iron my shirt.” I’m like, “The dry cleaner will do five shirts for £10, down the road. Just drop your shirts off there and have them done.”

Nisreene: I love that. Well, what else is in your kit?

Jennifer: Well, I have Topstick, which is actually toupee tape, and it’s great for, like, quick fixes. So if you have, like, a button-down shirt and it gapes open at, like, the bust area, you can close it there. Or if a shirt’s too low, you can close it up a bit without putting a stitch in it. If you have straps that are falling down, just stick them on really quick. It’s great and super powerful. I highly recommend that. It’s a top tip. Best brand for double-stick tape or body tape.

Nisreene: Topstick.

Jennifer: Yeah.

Nisreene: What about, like, gear? Like gadgets and stuff?

Jennifer: So I’ve been eyeing up this water bottle that… it apparently cleans the water to 99.9% of, like, all bacteria gone. And it’s a refillable water bottle, because I’m all about saving the planet, even though I travel so much, but you got to offset it somehow.

Nisreene: 100%. Yeah.

Jennifer: So it’s called LARQ. Apparently you can go to countries that have unclean water or, you know, water that’s not okay for you or I to drink. And so you can use their faucets and be able to drink the water because it purifies it in 30 seconds.

Nisreene: That’s super interesting. You know, I love that because I also bring my own refillable water bottle.

Jennifer: Yeah, I’m really intrigued about it. It has great reviews, so I’m into it. But I’m really not that techie. I love my Bose noise-canceling headphones, because I think I have really funny-shaped ears. So they’re the QuietComfort ones. So, like, AirPods don’t really stay in my ears, but the Bose QuietComfort headphones, they’re amazing on a flight – especially a long flight, because they cancel all noise and they’re really comfy that I can sleep in them, which is key on a long-haul, overnight flight.

Nisreene: Do they connect to the in-flight entertainment system? Do they have, like, a JAG or are they wireless?

Jennifer: So I always download my own stuff, like podcasts and, you know, whatever show I’m watching on Netflix or Amazon Prime.

Nisreene: I did see a gadget once, actually. I mean, classic, I found it on TikTok and I think it’s called AirFly. And it’s actually, like, a device that plugs into the in-flight entertainment system jack and then you wirelessly connect your headphones to that device.

Jennifer: Oh, that’s amazing.

Nisreene: So I obviously haven’t tried it out, but I’m really intrigued by it. Any other sort of, like, gadgets or travel essentials or things that you feel like you just absolutely have to have?

Jennifer: I always keep in my essentials kit bag, which isn’t very big, a world adapter as well. I just recently started doing this because I have about 20 because I always forget them. So now I just keep them in this bag, so I know this is a bag that will go with me every time I travel and I will not have to buy another one of these for, like, $25 at the airport. I’ll actually just have it packed with me on the go. Other than that, I have some travel socks that I always keep with me as well during the winter. Or, like, short-haul flights, I have a cashmere blend that I like to wear from Raey. R-A-E-Y. It’s on Matches and they’re amazing. Like, I’ve had them for a couple of years now and they haven’t worn out like a lot of cashmere-blend socks do. And then, of course, I have compression socks that I wear on long-haul flights – keep the blood flowing.

Nisreene: Not the most attractive, but really important. I wore them a lot when I was pregnant, so…

Jennifer: Yes.

Nisreene: And you know what? I think I’ll probably still wear them now. Yeah. Where are you in the neck-pillow space? I really feel like that has come a very long way. Like, there’s obviously the traditional sort of horseshoe shape, but now you’re seeing all sorts of weird ones where they, like, wrap around your head, they’re covering all aspects of it, you put your arms in some of them. It’s quite impressive. Where are you at on that spectrum, or are you a no-neck-pillow kind of gal?

Jennifer: I’m a no-neck-pillow girl. I cannot be bothered.

Nisreene: You’re just raw dogging it out there.

Jennifer: (Laughs) Yeah. I cannot be bothered to carry another thing with me when I go on a flight. I’m like bare minimum, just a face mask. I love a face mask on a flight because I used to get so dried out. And then, finally, I was like, obviously, just do a face mask. So yeah, now face-mask it up.

Nisreene: What’s your preferred brand?

Jennifer: Rodial is my favorite. I love their face masks. One of my friends works for them, so she always gives me, like, loads, stacks of them for free. So I just slap them on, chill out for the flight.

Nisreene: Yeah. Do you ever get any weird looks? Are people like, “What’s this lady up to?”

Jennifer: Still some men. But I think the women are probably just like, “Why didn’t I think of that? She’s going to come out glowing and I’ll be dehydrated.”

Nisreene: As a stylist, would you consider yourself the best at, like, packing and, you know, traveling and having all the gear and stuff like that?

Jennifer: Actually, I try to get my husband to let me pack for him when we go on trips together because it’s just appalling the way he packs. Like, he’s one of those people that just chucks everything into a suitcase and hopes it works out and that his outfits match. But I don’t have my outfits planned per se, but I like to have a tonal wardrobe or even just bright colors. So I could pack just a couple of pairs of shoes and they’ll match all of the outfits. Like, if you do all neutrals, you can mix and match and any outfit you put together will look fabulous. Like, you could even do blues and greens and tans. And you have if you have a mix of all of those colors, mixing and matching is so easy, then, when you’re traveling.

Nisreene: Well, this is the big question. Are we rolling or are we folding? How are those clothes getting into the suitcase?

Jennifer: I’m a roller only because you can fit more things into the suitcase. And that is the only reason I’m a roller, is space-saving techniques. Otherwise, I think it would be a folder because your clothes do come out looking a bit more crisp if you fold instead of rolling. But that’s where the handheld steamer comes in. That is my best friend on vacation.

Nisreene: Well, so, in addition to rolling, what other tips do you have in the packing space?

Jennifer: So, my other tips would be… Well, I think packing tonally is the key to being more concise and making sure that your accessories match everything in your case. So, you don’t want to pack a pair of shoes that only match one outfit that you packed. That is no good for anybody. You want to pack shoes that match everything in your case and then you have, you know, only three options or two options – however many shoes you decide to pack.

Nisreene: Where are you at in terms of packing cubes? Do you use them? Are you not into it? Like, what’s your perspective on that one?

Jennifer: I love the idea of packing cubes. I don’t currently use them, though. When I pack for clients, I have the outfits bagged by look. So I have, you know, a garment bag and it’s labeled with a picture and notes on what the event is. And, you know, it already has all the accessories inside of it. So I think I just, you know, with celebrities, you want it to be, like, as easy as possible for them so that they aren’t confused and there’s no question. Their assistant could go in there and just be like, “Okay, they’re going on David Letterman today” or whatever show, The Late Late Show. And they’re like, “This is The Late Late Show. It says Late Late Show on here. Here’s the garment bag and here’s the outfit.”

Nisreene: Well, that’s kind of like a packing cue. A garment bag is sort of like your version of a packing cube. So you’re obviously putting the outfits together and putting them in the garment bags. Are you actually putting those into a suitcase for them?

Jennifer: Mm-hmm, yeah.

Nisreene: Oh, wow.

Jennifer: So I got this suitcase…

Nisreene: I love celebrity stuff. Like, this is so fascinating. Okay, let’s talk about it. The outfit is in the garment bag. The accessories are in the garment bag, too. Are they, like, in pouches? Are they dangling on the hanger?

Jennifer: Yep. It’s very unglamorous how they’re packed, a lot of the time. So they’re in, like, little plastic bags so they don’t get scratched or anything, depending on what it is. If it’s breakable, it’ll be in, like, a bubble-wrap plastic bag and hung through the hanger in a drawstring bag so they’ll see what everything is along with the shoes and stuff. So everything, honestly, is, like, so laid out perfectly for them. I think it’s from my costume-design past. I worked at Gossip Girl as, like, one of my first jobs back in the day. And, yeah, I was part of, like, the continuity. I was a costume design assistant, so I did a lot of the continuity for the brand. So it was, like, writing out on the tags exactly what was used in each outfit. So it’d be, like, dress by Prada, bag by Chanel, you know, ring by Stephen Dweck or… You know, I’d have it all listed out and then hung in the clear plastic bag, and then in that bag, another bag of each individual piece of jewelry and stuff. So I think that’s where it comes from.

Nisreene: Okay. So everything’s in a garment bag. It’s in its own little pouch or it’s own little home. So, then, are we folding the garment bag to put it into the suitcase, or do you prefer to use actual, like, garment-bag suitcases?

Jennifer: We fold the garment bags, just in half.

Nisreene: Just in half. And then you put it in the suitcase just like that. Do you feel like that’s a good space saver or do you feel like that wastes space? Like, think of all of the rest of us. Like I am going on a vacation, right? And I’m seriously thinking about doing this because I… this is really vibing with me. So if each outfit’s in its own garment bag, how many garment bags can I fit in a regular suitcase?

Jennifer: It depends how big your suitcase is. We can fit quite a few. I don’t have a hard case. Well, I have some hard cases, but with my clients, I have these suitcases called It suitcases and they fold down flat. So, like, I have about eight of them because I usually juggle a lot of different jobs at once. So, they fold nearly completely flat. So when I’m not using them…

Nisreene: The suitcase folds flat?

Jennifer: Yeah. And then…

Nisreene: You’re, like, really blowing my mind. We’re only 10 minutes into this conversation. Okay. It’s called It brand?

Jennifer: Yeah.

Nisreene: I-T? Okay, okay.

Jennifer: So, I use those a lot because they round themselves out too, so I can fit quite a few… I would say probably up to, like, ten garment bags in there, which is quite a bit.

Nisreene: That’s a lot.

Jennifer: Yeah. So, very handy. And it’s nice for people that live in cities and might not have as much space to store big old clunky suitcases.

Nisreene: So do you use these IT brand suitcases for your own personal travel as well, or do you like others? Because I know there’s a lot of really high-end luggage out there. And I, personally, am not a believer that it’s totally worth it. Like, in my mind, you want a luggage that is already light, because if you’re packing a lot of stuff, you don’t want the actual empty suitcase to take up half of the allotted weight, right? But, then, one that just has smooth wheels. And that’s, frankly, all I personally really care about. Where are you at in that discussion?

Jennifer: Well, I recently just got an Away suitcase that has the portable charger in it. And very keen on that, because I feel like I’m one of those people that will forget to charge their phone at night because I’m thinking about something else and just forget to plug it in and then I’m, like, screwed. So that’s really handy and I’m kind of obsessed with it, but it’s just my carry-on. And then I have, like, CALPAK luggage for, you know, everyday travel. But I think fancy luggage is really cool. Like, you know the brand Globe-Trotter?

Nisreene: I do. That stuff is cute.

Jennifer: It’s so cute, right? Like, one day I will have some Globe-Trotter. Like, it’s so adorable and all the different themes they have. They have the Disney theme, they have, you know, just all these fun collaborations that they do. But yeah, it’s really expensive, especially for me. I travel so much, it’s just going to get really banged up

Nisreene: Yeah. When you travel, like, personally, for fun, are you a carry-on type of person or do you typically check your luggage?

Jennifer: Ideally, I carry on as much as possible.

Nisreene: What if you’re going for a week?

Jennifer: If it’s a summer or hot destination, carry-on for sure. I just am not interested in checking bags. I’m one of those people that once I get there, I just want to go. I don’t feel like waiting for my luggage. I’m keen on walking off the plane.

Nisreene: Yeah, I’m keen on that too. But I’m, like, a chronic over-packer. What tips do you have for people like me, you know?

Jennifer: I think this circles back to wearing neutrals again or wearing something that’s tonal. So you can mix and match different pieces that you packed. So you could pack, you know, eight pieces instead of 16 because you can mix and match and wear them again. And when you steam – going back to steaming – it basically cleans the outfit for you. So, like, it gets rid of all of those germs and it’s basically like washing your shirt.

Nisreene: What if you’re sort of traveling to a place that’s going to be warm and cold? Do you know what I mean? Like, I feel like you go to a lot of places where it’s, you know, almost like a desert environment where it’s hot during the day, but then it drops to 50 degrees at night and it’s freezing. How do you… what’s your balance there?

Jennifer: Loads of layering. So I will always be on a plane in layers if it’s going to be cold, only because the plane is normally really cold. So it’s really, really nice to wear those layers on the flight if you’re going to have a carry-on. And I always find that super handy – and you only need, like, one jacket or one cardigan. You don’t need to have a different jacket or cardigan for each outfit because you’re packing a tonal wardrobe. So that jacket or cardigan will match everything else that you have in your suitcase.

Nisreene: I think maybe people get afraid that, like, other people are going to notice that they’re re-wearing things. As a professional stylist, do you think people actually pay attention to that kind of stuff? Or, like, how does that factor into when you’re packing? Like, are you like, “I’m going to re-wear, I don’t care”? I feel like French people, by the way, will re-wear the same outfit, like, three days in a row and they don’t care and they still look, you know, fabulous and chic, but Americans are just really averse to re-wearing. And I think there’s also a lot of outfit checkers out there. We think that there are. What do you think?

Jennifer: Yeah, I just wonder who they think is going to notice. Maybe people on social media, because the people at the patisserie down the road aren’t going to remember what you wore the day before. I wouldn’t be worried about that. And you’re being smart about what you’re packing. There are some amazing brands out there. For instance, the Frankie Shop. They’re such good quality pieces and they do, like, oversize button-downs and they have, like, matching sets. So you could buy the matching shorts and the matching pants, matching bralettes – just, basically, matching everything. So you could wear that oversize shirt over a bathing suit as, like, a cover-up or you can have it tucked into a pair of shorts or you can wear it with the matching pants. The button-down oversize shirt is, like, all the rage at the moment, and it’s in good reason because it’s so versatile.

Nisreene: I just bought three of them, actually.

Jennifer: Did you?

Nisreene: I bought a white one, a blue one, and a pink one that has matching shorts. So I feel really validated by this conversation, to be honest. So that’s great.

Jennifer: I’m glad.

Nisreene: What about packing for cold trips? Like, a trip to… you’re going skiing. Because I feel like that is a really stressful time, because every… You’re packing sweaters and, like, ski gear, everything just gets really bulky and super heavy. Any tips for cold weather trips?

Jennifer: So for cold weather, I always wear layers and I have black thermals that I wear underneath everything and I wear that on the plane as well. I have an amazing, like, cashmere tracksuit set that looks very chic, but also looks, you know… It is comfy, it doesn’t look comfy. It is comfy. Allude is the brand and they do, like, half-zips as well. And I think it’s just so nice to, like, wear on a plane. So I highly recommend that. And then, packing, I’ll always wear the, like, long underwear or the layers underneath while on the plane. Or if it’s a long-haul, I’ll pack it because they roll up really, really tiny and you could put them on when you’re going skiing. I use Falke a lot – F-A-L-K-E – for my clients and for myself. And, also, I have this amazing Wolford bodysuit that’s like a turtleneck. And I think it looks cool underneath anything, really. You could have, like, a loose-fitting cardigan on, a V-neck cardigan would look nice. And that’s just, like, one item that you could re-wear and re-wear and re-wear. Oh! And, also, when you’re packing, your biggest boots that you’re packing, wear those on the plane – which I know is such a pain when you’re going through security and you have to take your shoes off, but it’s worth it because you have so much more space in your luggage.

Nisreene: Yeah, that’s a really good tip. So I want to go back to – you know, you talked about the garment bag trick that you’re using. What other packing tricks do you have or, like, special equipment that you use for any of these trips?

Jennifer: When I’m packing for myself, I have a jewelry cube, which is basically like a travel jewelry case. And that’s really handy because it does what the plastic bag tip does, but in a fancier way, because I don’t need to know exactly what necklace goes with what outfit – I’ll pack accessories that match all of the outfits I have packed.

Nisreene: What about for men? I’m sure you have, like, a decent amount of male clients as well. Does your approach to packing or how you style them, does that change at all?

Jennifer: A lot of the time with womenswear, we – if it’s celebrities, especially, they will not want to wear the same shoes with several different outfits. So everything’s bagged separately. But for menswear, they’re much more keen on just having one pair of shoes or, like, two pairs of shoes. One belt for the three full days they might be in, like, the Italian Riviera for like a wedding. They might only want, yeah, one belt for the entire time and then one pair of shoes. They can make it work for that.

Nisreene: Can I ask you to spill a little bit of tea for us? You don’t have to tell me the names, but what’s, like, the weirdest thing you’ve ever had to pack for a celebrity? Or, like, has anybody asked you to pack, like, a really weird gadget or something like that?

Jennifer: If I have a client who is breastfeeding, I will always pack breast pads. When I was, you know, breastfeeding my kids, it was the one thing that sometimes you could forget to pack for yourself, but you don’t want to have milk seeping through your outfit. So just slot those in with, you know, their kit bag that I send with them. I actually just did a TV show for Amazon Prime, and there’s this one episode, one of my clients is on it, and I grabbed her from backstage because she has rings of breast milk on her top.

Nisreene: Oh no!

Jennifer: And so you see me backstage, like, blow drying her top right before she has to go back onto stage. And it’s just like those moments that you don’t want to happen when I’m, especially, not there. Stuff like that that people might not think of. I always pack tampons for women just in case they have, like, a surprise period. I always pack period pants as well in nude, because those are just handy if they’re expecting their period and, you know, don’t want to wear something for it. Otherwise, nothing else that is that out of the ordinary.

Nisreene: Are there any, sort of, travel gear or accessories that you swear by when you’re traveling with your kids? You have one child or two or…? What’s your family situation?

Jennifer: I have two. I had them very close together. I have a daughter, Waverly. She is three. She’ll be four in August. And a son, Hudson.

Nisreene: Aw, nice.

Jennifer: Very New-York-centric names.

Nisreene: Yeah. So what travel gear do you, like, swear by when you’re traveling with your kids?

Jennifer: Well, back when I was breastfeeding, I love the Elvie pumps, because I went straight back to work. So, I didn’t take any time off after the kids. I just kind of like made do and would, like, have them strapped to me on set and just bring them around for fittings, just dangling off me. So I would have, like, the Elvie pumps when they couldn’t be with me so I could pump and it’s, you know, not attached to anything. And just stick them in your bra and it has a little app on your phone. It’s so, so handy, so good for any new moms. It’s worth the investment, ’cause I know they’re not very cheap, but it’s something that I highly recommend

Nisreene: Well, before we go, if you had to, like, if there was one travel gear item that you absolutely cannot live without. Like you’re traveling, you’re getting on a plane, you can only take one thing in addition to your suitcase. What are you taking with you?

Jennifer: Ooh. This is such a good question. I think I’m going back to the steamer because I think it just makes such a difference in pictures when you’re looking crisp and fresh and it just makes a world of difference. So I think I would say my steamer. I am obsessed with my little handheld steamer.

Nisreene: Yeah. The point about it also freshening up your clothes and killing germs is actually something that I never thought about. But I do get really grossed out. Like, I feel like when I wear like a jacket on the plane and then when I get to my destination, I’m like, “Ugh, I don’t want to wear this.” Like, the plane is such a disgusting place, my daughter dropped it on the floor or whatever. But, so now I’m like, “Well, maybe I’ll start to bring the steamer with me and then I won’t have any, like, stress about it.”

Jennifer: Yeah, they’re so tiny now, too. It’s literally the size of a water bottle – or a big water bottle. You know, like a 750ml water bottle. But so worth the space that they take up. Highly recommend it to everyone and they’re cheap too.

Nisreene: Jennifer has an amazing Amazon shopping list and we’ve gone ahead and included that on the blog for all of you to reference.

Jennifer: Yeah, ’cause I have, like, pre-threaded needles. There’s loads of little things that I always keep in my, like, little essentials kit bag that I bring around.

Nisreene: That’s great. So, Jen, you’ve got so many amazing tips, obviously, and it sounds like you live an absolutely fabulous life. Where can people, sort of, follow your adventures or learn more about your work? Or maybe someone just wants to, like, live it up and let you style them for their next vacation.

Jennifer: You can find me on Instagram at Jennifer Michalski-Bray Style and I have a personal styling masterclass which just launched. It is at So check it out.

Nisreene: Thank you so much for coming on the show today. It has been an absolute pleasure having you.

Jennifer: Oh, thank you for having me. It’s been so fun.

[Musical interlude]

Nisreene: My favorite piece of information that I learned in this one was using a steamer to not only keep your clothes fresh and crisp-looking, but to also kill all that nasty, grimy travel bacteria that might happen when you’re wearing something on the plane or just throughout your travels. So it’s definitely something that I know I’m going to do from here on out.

What’s your favorite travel gear item? Tell us. We’re @Expedia and @PRX.

For more info on episodes, guests, and to find travel inspiration, be sure to visit Out Travel The System’s blog at

I want to thank our listeners so much for joining us today. I also want to thank celebrity stylist extraordinaire Jennifer Michalski-Bray for all of her great tips. If you have any questions for me or comments or thoughts, of course, be sure to hit me up. You can DM us on @Expedia. And be sure to follow, subscribe and share so that you don’t miss an episode.

Out Travel The System is brought to you by Expedia, with special thanks to PRX and Sonic Union. I’m the Executive Producer and your host, Nisreene Atassi. Special thanks to the following:

Additional writing by Rachel Sullivan
Producer Rishika Sharma
Associate Producers Syma Mohammed and Nathanael Taylor
Production Assistant is Alex Thiel and Carolina Garrigo
Theme music and original composition by Kevin J Simon
Music edit, sound design, and mix by Rob Ballingall
Music supervision by Justin Morris
Executive Producer and Writer Halle Petro
PRX Executive Producer Jocelyn Gonzalez

Out Travel The System is recorded with Sonic Union in New York City.

Be sure to join us next week as we talk all about small town American destinations with Matt Hranek. Get ready for some solid Americana.

Till next time, this is your host, Nisreene Atassi, for Out Travel The System. Find us on Apple Podcasts or wherever you listen. Happy travels!